


trying it out

by hey_you_with_the_face



Series: NC-17 Novelties [2]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, F/M, Married Couple, Pegging, Sex Shop AU, Sex Toys, Slight hand kink, Strap-Ons
Language: English
Status: Completed
Published: 2017-09-14
Updated: 2017-09-14
Packaged: 2018-12-27 20:13:42
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,873
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12088530
Author URL: https://archiveofourown.org/users/hey_you_with_the_face/pseuds/hey_you_with_the_face
Summary: One night during a tipsy conversation, Sam reveals that there's something he's always wanted to try. Luckily for him, Eileen would love nothing more that to help him out...





	trying it out

**Author's Note:**

> And another bingo square off the list; this time it was pegging.
> 
> This is set in my DCJ sex shop AU (which I recently turned into series since there's another story for this 'verse in the works) so that's a nice bonus. :)

Eileen was strangely fascinated by Sam’s hands.

It probably had something to do with the unlikely grace in them. They were large, broad hands that she knew had a lot of power in them but yet they moved elegantly whether he was signing or just gesturing in general. She thought they were beautiful, just like the rest of the man to which they were attached.

Though it also didn’t hurt that she knew exactly what those hands were capable of when it came to their time alone. 

How they could tangle into her hair or slide hotly up and down her bare back. How they caressed her thighs or other more sensitive areas. She’d always assumed those were most erotic things she could ever see those hands doing but now…

Now she knew how wrong she’d been.

At the moment, Sam hands were tangled in the thoroughly rumpled sheets of their bed. He was gripping the fabric so tightly the tendons showed beneath the skin. Under normal circumstances, Eileen wouldn’t have been able to look away from those gorgeous hands but these weren’t normal circumstances. 

She ran a hand soothingly down the blazingly hot skin of Sam’s chest and leaned forward so she was pressed against him and could lay a line of kisses across one collarbone. Sam’s eyes were squeezed shut and his mouth was dropped open and his breathing was heavy, puffs of heated air tickled her skin. Needing to make sure Sam was ready for the next part, Eileen caressed his face lightly in an unspoken question.

Sam opened his eyes and looked up at her. He nodded earnestly and she saw his lips forming a chanting “Yes, yes please.”

Giving one last lingering kiss to his jaw, Eileen leaned back and poured more lube into her hand and reached down to liberally slick up the strap on secured around her hips. She continued to massage his thigh soothingly as she bent his legs and placed the tip of the toy to Sam’s carefully prepped ass. She slowly pressed forward. 

Eileen shivered as she felt the deep vibrations under her palm that were undoubtedly Sam groaning in pleasure if the expression on his face was anything to go by. Eileen stilled for a moment, giving Sam time to adjust to the feeling of being penetrated. When he nodded again, she began moving at a slow, careful pace. 

She was determined to make this experience as amazing as possible for Sam.

 

When Sam had first admitted that he was interested in having Eileen fuck him, she had thought it was just a throw away thought brought on by one of their late night talks. They’d been drinking a bit and talking about the kinky things they had done in the past and were interest in trying someday. Eileen would confess to feeling more than a bit shocked when Sam had haltingly tried sign out what he’d always wanted to try and, failing that either due to nerves or being mostly drunk, ended up writing it out on a notepad.

 _I’ve always thought I’d like pegging_.

Sam had quickly tore out the page and changed to subject after this admission even though Eileen had tried to talk about it, to reassure him that she didn’t find his fantasy strange or abnormal, and they hadn’t talked about that night for some time. Not to say that Eileen hadn’t thought about it or noticed that Sam started acting more reserved, probably misinterpreting her contemplative mood as one of disgust or disinterest. On the surface everything seemed normal, their lives moved on and they still were intimate but something was just slightly off most of the time and Eileen didn’t like it. She wanted things to go back to being relaxed.

Which was why she’d sought out the help of her unofficial brother in law and ordered a strap on.

It really paid to have a brother in law who ran a sex shop with his two boyfriends. Dean’s boyfriend Cas had been happy to help her out and understood the need to keep it from Jimmy and Dean. It wasn’t that they didn’t trust them, Eileen just felt that it was Sam’s secret to share and keeping the information as guarded as possible was less exposing. The only reason she told Cas was so that she was sure she was getting a quality toy as well as sound advice on using it. In no time at all, they had found the perfect toy for them and after a thorough tutorial and a promise to slip him a review of it on the down low, Cas had sent her on her way with his blessing.

Approaching Sam about it had been an entirely different matter.

_“You bought a what?!” Sam’s hands had flown in front of him as his jaw dropped at her announcement._

_“You said you were interested in pegging, so I bought a strap on,” she’d answered calmly. Eileen had pointed to the bag sitting on her dresser._

_If it hadn’t been for the fact Eileen had been worried about Sam’s adverse reaction to her news, she would have thought the expression on his face had been hilarious. Sam had made an excuse about starting dinner, leaving her to wonder if she’d made a mistake._

It had taken some time but eventually, with a lot of coaxing and reassurance, Eileen had gotten Sam to stow his embarrassment and admit that he wanted to try. She told him that it was nothing to be ashamed of and that she thought it would be fun for both of them to at least try. If Sam didn’t like it, they would stop and never do it again.

They’d agreed to try that weekend.

Eileen had taken extreme care to follow all the instructions Cas had given her. Sam had done his own research and insisted on showering alone beforehand and Eileen had continued along this line by proposing a nice joint bath afterward. The nice soak in the bathtub seemed to help relax him but Eileen could still sense some tension. 

Luckily she’d already planned on a massage. 

She’d made sure to thoroughly loosen Sam’s tensed muscles until he was a relaxed lump and, quite smoothly she thought, introduced the preparatory stage. At the pleasured look on Sam’s face as she’d started fingering him, Eileen had relaxed too. Sam was definitely enjoying himself and she knew she was definitely enjoying the satisfaction of seeing Sam feel so good. Every pleasured tick of his face had sent a jolt of excitement through her.

Soon Sam’s hips were rocking down onto her fingers but, in deference to the advice she’d been given, she hadn’t rushed into anything. It wasn’t until she was absolutely sure he could take the beginner strap on that Cas had recommended, which had been rated a hearty eight on the shop’s scale (aka “Go Forth and Fuck”), that she’d finally given into Sam’s insistent demands. 

And here they were.

Eileen quickly caught on to what Sam enjoyed, noticing that his eyes squeezed shut and she could feel his chest rumble under her palm when she pressed in close and ground her hips in shallow thrusts. Sweat broke out all over Sam’s body as he squirmed underneath her, trying to make her go harder but Eileen stuck to her pace even though she wanted to speed up too. Every slow grind that had to be rubbing against Sam’s prostate was also massaging the base of the strap on against her clit until she was breathing heavily with each movement. 

Her thighs strained as she kept fucking into Sam but it was easy to ignore the slight burn in the muscle when she could be distracted by the sight of Sam breaking down into a panting, writhing mess. One of his hands still clutched at the sheets while the other reached down to start touching his cock which had been laying neglected on his heaving stomach, leaking precome steadily onto his skin. Eileen shivered as she realized she’d never seen him this wet before and that she was causing it. 

She looked up to see Sam’s mouth moving. What limited part of her brain that wasn’t currently focused on rocking her husband’s world worked to decipher what he was saying and a shot of heat raced down her spine when she realized Sam was chanting her name in between begging her to fuck him harder. Unable to deny him, Eileen pumped her hips forward harder, feeling a deep groan burst out of Sam as his hand sped up. Sam was teetering at the edge of the cliff and Eileen was eager to see what he looked liked.

Reaching down, her hand joined Sam’s in stroking him; Sam shivered and sucked in a heaving breath, his eyes shooting open to meet Eileen’s. The heated desperation in Sam’s eyes was intoxicating. His hips were rocking haltingly up into their hands and down on to the strap on; his movements jerky and frantic. Eileen could feel Sam’s heartbeat racing beneath her hand along with the steadily increasing rumble of his groans.

Eileen was so lost in the feel of Sam writhing against her, the sensations of his pleasured sounds and the sight of him falling apart that she was caught by surprise when Sam suddenly seized up. He managed to keep his eyes on hers for a brief moment before they slammed shut as his back arched and his cock throbbed in their hands, come spurting out to drip over their fingers. Eileen, body already tingling hotly after watching Sam come, was delightfully stunned when one final forward grind against the strap on triggered her own orgasm and she game with a sharp gasp.

Arms shaking, Eileen managed not to fall on top of Sam; not because she was worried she would hurt but because she had to take care of him. Sam was laying sprawled out on the bed, his limbs loose and pliant; he twitched slightly as she pulled the toy out but other than that he remained a blissed out heap.

It would be a bald faced lie to say Eileen didn’t feel a little bit proud at this.

She quickly and efficiently cleaned Sam up, making sure he was comfortable before putting the toy aside and crawling onto the bed. It took a bit of doing to pull the blankets from underneath Sam’s legs, especially since he wasn’t exactly responsive at the moment besides a few twitches, but eventually she had them covered. Eileen snuggled up to his side and pulled his arm around her shoulders. 

Sam still hadn’t made a move to say anything and she was starting to get nervous. What if she had misinterpreted his reaction during? Maybe he really hadn’t enjoyed it at all.

Licking her lips while her heart pounded, Eileen shifted so she could awkwardly sign. “Did you like it?”

A few tense minutes passed before she felt Sam move, his arm pulling away from her shoulders so he could sign back. He was smiling tiredly at her and she could see a mischievous light in his eyes that put her at ease.

“We are definitely doing that again.”

**Author's Note:**

> And there we have it, sweet yet sexy Saileen pegging sex. I was really excited to finish this square since I'm now only one square from getting an actual bingo on my card now and I've already started the square I'll need to fill for that :D


End file.
